Crooked Media's Jon Lovett Is Ready For A New President

In the wake of Donald Trump’s election as the 45th President of the United States, Jon Lovett realized he “didn't want to go back to just being a writer,” and that he had actually “felt the pull of politics” for some time. That’s when the former speechwriter for President Barack Obama and Hillary Clinton when she was a Senator joined forces with his fellow former White House colleagues, Jon Favreau and Tommy Vietor, who felt the same pull in the post-election haze of a Clinton defeat.

The trio set out to build a media entity that challenged the typical political punditry of cable news.

“Because even before Trump won, for us there was a real frustration about the political conversation,” Lovett said. “The punditry around politics felt broken… and you come away from those shows, and Twitter and Facebook... feeling like you’re treated less like a frustrated participant and more like a cynical observer. You don't hear about what the issues are, you hear how the issues are playing. You don't hear about what what politicians will do for people, you hear what politicians will do to win.”

In January 2017, they launched Crooked Media, a podcast network and news and opinion website.

“We wanted to see what it would look like to have a conversation that was about informing people, entertaining people, but also inspiring action,” he continued, “that talked not just about what's broken, but what people can do about it.”

Just two years later, Crooked Media boasts a suite of 10 podcasts, a four-part HBO series during the last midterm election cycle, and a consistent trove of political editorials on its site. Ahead of a national tour for both the Pod Save America and Lovett or Leave It podcasts, we spoke with Lovett in the Crooked Media Hollywood offices about the network, what political issues we should pay attention to in 2019 and what audiences can expect when his podcasts come to their hometowns, starting February 6 in Washington, D.C.

What do you remember most about forming the idea of what Crooked Media could be?

I remember in the weeks after the November election, Jon, Tommy, and I were reaching out to a lot of people talking about how to launch a business, which we knew nothing about. We did not have a business plan. We were doing a lot of brainstorming on names for things, what should this podcast be called, what are we going to do, how's it going to work? And how long can we do this if it doesn't make money?

But I think in those weeks, we wanted to take this bet that there were a lot of people like us, people that felt frustrated with the political conversation, and people that wanted to be more involved than they were, that Trump winning was a wake-up call for a lot of people and maybe it shouldn't have been. I think a lot of what Trump represents is how bad things can get, but also how bad things were that we didn't see. Those two things together, I think, have activated a lot of people.

Also, honestly, I think a big part of this is it's made a lot of people who weren't disenfranchised understand what it means to be disenfranchised, what it means to feel disenfranchised, what it means to feel disempowered. And I think that was scary for a lot of people who had a lot of assumptions that Trump laid bare.

Why was it important to add other shows, like Keep It or Pod Save the People to the roster with Pod Save America?

We were three white guys that were like, “We need to have a big conversation,” but it's a conversation that's not just for us, and not just to us. And so, we have been building this bigger network with people like Ana Marie Cox, DeRay [Mckesson], and Ira [Madison III]. And we launched Lovett Or Leave It, which is a comedy show. One of the things I'm most proud of of Lovett or Leave It is that it's really become a forum for diverse, young, and up-and-coming comedians, writers, journalists, and academics and also a place where you can have a conversation where there's a comedian, a writer, a socialist professor all talking about the news. It's exciting to be part of something that doesn't exist in other places.

You said that one of the intentions of Crooked Media was to drive people to action. How did that manifest itself during the midterms and beyond?

In 2018, we obviously believed that winning the House was this incredibly important mission because of the kind of signal would that send. So, we put a lot of our focus on that, and we built this tool called Vote Save America, which I believe it's fair to say is the first of its kind, because it combined not only finding out about your polling place, not only being able to check if you're registered to vote, but also finding opportunities to volunteer, ways to donate and other ways to help. It really fit with this mission of informing people about issues in a funny and entertaining way, but also giving them the tools to participate.

We raised a lot of money. People signed up and did volunteer shifts. And that's the single most rewarding thing of the past two years. We're having a conversation about politics the way we would, but we figured out a way to tap into a lot of this fear, and also this enthusiasm. Our bet from the beginning was that the opposite of cynicism isn't false hope, or false optimism. It's participation. And I think one of the lessons of Trump winning is, there's no one else who's going to do it, that if you don't get in it, we cede the field to the worst elements in our country.

For those who've never seen the podcasts live and are only audio audience members, what can they expect?

The live shows are pretty wild. It mostly comes across on the podcast, but there's an energy in that room that's really fun. It's the difference between, I think, being at a concert and listening to a concert. And there's something about being part of a community of people that you don't feel when it's in your ear.

At some point, there will be a final day that Trump is in office...

That to me is really exciting, because when I get down and when I get angry, like the thing I always think about is there will be a last day that Trump is president. And on that day, we'll no longer altogether be focused on trying to stop something awful. We'll actually all be paying attention, and have the chance to do something really good. Because Trump is a symptom of political rot, of cultural rot, of a fundamental failure on the part of every major institution in this country, and that won't go away.

Those holes that he managed to slink through, they don't close the day he leaves office. It's going to be up to us to figure out how to close them. And my hope is that all of this attentiveness — it will not last, but when we have it, we can use it. And that is to me the part of the last two years that has made me the most hopeful.

I think there's the congressional conversation and there is the organizing conversation and there’s the presidential conversation. For the presidential conversation, there are three parts of it, and I'm only really interested in one of them right now, and only two of them ever. There is who's electable. Connected to that, there is who's the best person to go toe-to-toe with Trump. And then the third is about what do these people stand for. To me, the electability conversation is one we should just ... I don't know what it means to be electable and I don't think anybody really does. How many people thought Trump was electable? If you told people in 2007 that Barack Obama was electable, they would've told you you were wrong. So, I think the electability conversation is very, very silly.

There's these two things that are going to be on a lot of people's minds. Obviously there's policy, but one of them is, "Who's going to go toe-to-toe with Trump?" To me, there'll be time for that. I don't think it's unimportant, and we need to think about it, … but the best thing we can do is [focus on who understands] that you can't sound like the Democrats we had before. Because the Democrats who sounded like the Democrats we had before are part of the path that led us to Donald Trump seeing an opening for himself.

And to me, then the next question is, who would you like if Donald Trump never came along? Like, who do you think would be a great president?

And endless debates about 2016 are not particularly helpful because I think a basic assumption we should all have is that someone like Donald Trump should have never gotten close. Like, Hillary Clinton barely lost, and there are really unfair reasons that she did. But, if she had barely won, that'd have been terrifying too. So to me it's like those are the two things: Who do you believe in, and who is speaking about policy in a way that you think rises to this moment?

Are there any particular issues that you think not enough people are paying attention to?

I think there's been a lot of talk about economic inequality. Democrats and Republicans have presented two options to the fact that we've seen incredible concentration of corporate wealth, that consumers lack power in the marketplace and that workers lack power in the marketplace. What's their answer?

Republicans' answer has been to make matters worse, concentrate wealth even further. Democrats have struggled to offer answers commensurate with the scale of the challenge. But that’s what I’m interested in… [is candidates] speaking to that fundamental question about corporate power and not just about it as a problem, which Democrats are very good at. But saying, "And here's what we'll do, even if it pisses people off, even if it hurts our base of wealthy donors, even if Republicans try to convince people that we're socialist, even if Republicans lie and say that we'll destroy the economy and destroy American business."

The government is now in its longest shutdown in history. What should be our concerns?

What happened with this shutdown is, Republicans and Democrats passed a funding bill and then in between that funding bill passing the Senate and becoming law, Donald Trump pitched a fit — because Ann Coulter was mad at him, because Nancy Pelosi was getting a lot of attention, because Democrats had won something, and because he looks around and he sees stories about him, and they're about Mueller, they're about crimes, they're about Democrats winning, they're about him being unpopular.

To me, the most important thing is we can't give into that kind of governing. If Donald Trump can shutdown the government, and Democrats then give him what he wants — not only let him govern in this impulsive, childish, vicious way, but also give into his policy preferences — that's the ballgame. What's stopping him from doing it five more times? He can always do it. He has no compunction, he doesn't care about people, he doesn't care about the 800,000 furloughed workers, he doesn't care about the Native Americans not getting services, he doesn't care about the fact that food stamps may not go out, he doesn't care that tax refunds don't go out. He doesn't give a shit.

But, his fellow Republicans do. They do. So, we can't give into this. And I think what's good is the Democrats have been pretty strong and pretty united, and that has to remain the case. And I would say also to people reading this, please do not go into Joshua Tree National Park and cut down Joshua trees. I have no basis with which to say this, but I do not believe a single gay person is responsible.

I think you'd be correct.

The government shutdown is the longest shutdown in American history. It is hurting real people, it will continue to do so. But it's a reminder that every day Donald Trump is president is hurting people. And the most important thing we can do is be unequivocal in defense of what we believe in, and we don't believe we need a wall.

Purchase tickets for live recordings of Lovett Or Leave It and Pod Save Americahere.